4.2.1.84: nitrile hydratase
This is an abbreviated version!
For detailed information about nitrile hydratase, go to the full flat file.
Word Map on EC 4.2.1.84
-
4.2.1.84
-
rhodococcus
-
amidase
-
acrylamide
-
rhodochrous
-
erythropolis
-
synthesis
-
feiii
-
low-spin
-
fe-type
-
non-heme
-
sulfenic
-
benzonitrile
-
pseudonocardia
-
sulfinate
-
propionamide
-
cysteine-sulfinic
-
neonicotinoid
-
ruber
-
propionitrile
-
cgmcc
-
thiacloprid
-
carboxamido
-
aldoxime
-
indole-3-acetonitrile
-
chlororaphis
-
metallochaperone
-
industry
-
pharmacology
-
degradation
-
environmental protection
-
analysis
- 4.2.1.84
- rhodococcus
- amidase
- acrylamide
- rhodochrous
- erythropolis
- synthesis
-
feiii
-
low-spin
-
fe-type
-
non-heme
-
sulfenic
- benzonitrile
- pseudonocardia
-
sulfinate
- propionamide
-
cysteine-sulfinic
-
neonicotinoid
- ruber
- propionitrile
-
cgmcc
- thiacloprid
-
carboxamido
- aldoxime
- indole-3-acetonitrile
- chlororaphis
-
metallochaperone
- industry
- pharmacology
- degradation
- environmental protection
- analysis
Reaction
Synonyms
3-cyanopyridine hydratase, acrylonitrile hydratase, aliphatic nitrile hydratase, ANHase, Co-type NHase, Co-type nitrile hydratase, cobalt-containing nitrile hydratase, CoIII-NHase, CtNHase, Fe-NHase, H-NHase, H-nitrilase, high-molecular mass nitrile hydratase, high-molecular weight nitrile hydratase, hydratase, nitrile, iron-type nitrile hydratase, L-Nhase, L-nitrilase, low-molecular mass nitrile hydratase, low-molecular weight nitrile hydratase, MbNHase, NHase, NHaseK, NI1 NHase, NilCo, NilFe, nitrilase, nitrile hydratase, NthAB, PaNit, ppNHase, ReNHase, TNHase, toyocamycin nitrile hydratase
ECTree
4.2.1.84 nitrile hydrataseAdvanced search results
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results (Substrates Products
Substrates Products on EC 4.2.1.84 - nitrile hydratase
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SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(1R,3R)-2,2-dibromo-3-phenylcyclopropanecarbonitrile + H2O
(1R,3R)-2,2-dibromo-3-phenylcyclopropanecarbamide
(1S,3S)-2,2-dimethyl-3-phenylcyclopropanecarbonitrile + H2O
(1S,3S)-2,2-dimethyl-3-phenylcyclopropanecarbamide
(2R)-2-hydroxy-3-methylbutanenitrile + H2O
(2R)-2-hydroxy-3-methylbutanamide
-
-
-
-
?
(2R)-2-hydroxybut-3-enenitrile + H2O
(2R)-2-hydroxybut-3-enamide
-
-
-
-
?
(2R)-2-hydroxybutanenitrile + H2O
(2R)-2-hydroxybutanamide
-
-
-
-
?
(2R)-2-hydroxyhexanenitrile + H2O
(2R)-2-hydroxyhexanamide
-
-
-
-
?
(2R)-2-hydroxypentanenitrile + H2O
(2R)-2-hydroxypentanamide
-
-
-
-
?
(R)-2-chloromandelonitrile + H2O
(R)-2-chloromandelamide
at 100% the rate of 2-hydroxy-4-phenylbutyronitrile
-
-
?
(S)-3-benzoyloxypentanedinitrile + H2O
3-amino-1-(2-amino-2-oxoethyl)-3-oxopropyl benzoate
-
substrate conversion: 38.5%, enantiomeric excess: 68.2
-
-
r
1-(4-bromo-phenyl)-aziridine-2-carbonitrile + H2O
1-(4-bromophenyl)aziridine-2-carboxamide
-
-
-
-
r
1-(4-methoxy-phenyl)-aziridine-2-carbonitrile + H2O
1-(4-methoxyphenyl)aziridine-2-carboxamide
-
-
-
-
r
17alpha-cyanomethyl-17beta-hydroxy-estra-4,9-dien-3-one + H2O
17alpha-acetamido-estra-1,3,5(10),9(11)-tetraene-3,17beta-diol
-
the steroidal group is metabolized very slowly
-
?
2(R)-(4-chlorophenyl)-3-methylbutyronitrile + H2O
2(R)-(4-chloro-phenyl)-3-methyl-butyramide
2(S)-(4-chlorophenyl)-3-methylbutyronitrile + H2O
2(S)-(4-chloro-phenyl)-3-methyl-butyramide
2,3,4,5,6-pentafluorobenzonitrile + H2O
2,3,4,5,6-pentafluorobenzamide
-
-
-
-
?
2,3-dihydro-benzo(1,4)dioxine-2-carbonitrile + H2O
2,3-dihydro-1,4-benzodioxine-2-carboxamide
-
substrate conversion: 45.1%, enantiomeric excess: 0
-
-
r
2-aminopropionitrile + H2O
2-aminopropionic acid amide
-
90% of the activity with propionitrile
-
-
?
2-chlorobenzaldehyde + HCN + H2O
(R)-2-chloromandelonitrile
-
-
90% conversion to alpha-hydroxy nitrile
-
?
2-fluorobenzaldehyde + HCN + H2O
? + H2O
-
-
100% conversion to alpha-hydroxy nitrile
-
?
2-hydroxy-4-phenylbutyronitrile + H2O
2-hydroxy-4-phenylbutyramide
-
-
-
?
2-hydroxymethyl-3-phenyl-propionitrile + H2O
2-benzyl-3-hydroxypropanamide
-
-
-
-
r
2-methoxymethyl-3-phenyl-propionitrile + H2O
2-benzyl-3-methoxypropanamide
-
-
-
-
r
2-nitrobenzaldehyde + HCN + H2O
? + H2O
-
-
20% conversion to alpha-hydroxy nitrile
-
?
2-phenylbutyronitrile + H2O
2-phenylbutyramide
-
used as well as phenylacetonitrile
-
-
?
2-phenylglycinonitrile + H2O
aminoacetamide
-
used as well as phenylacetonitrile
-
-
?
3-(trifluoromethyl)pyridine-4-carbonitrile + H2O
3-(trifluoromethyl)pyridine-4-carboxamide
-
-
-
-
ir
3-allyloxy-4-phenyl-butyronitrile + H2O
4-phenyl-3-(prop-2-en-1-yloxy)butanamide
-
-
-
-
r
3-aminopropionitrile + H2O
3-aminopropionic acid amide
-
2.7% of the activity with propionitrile
-
-
?
3-benzyloxy-3-vinyl-propionitrile + H2O
3-(benzyloxy)pent-4-enamide
-
-
-
-
r
3-bromobenzonitrile + H2O
3-bromobenzamide
-
5% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
?
3-chlorobenzaldehyde + HCN + H2O
? + H2O
-
-
100% conversion to alpha-hydroxy nitrile
-
?
3-fluorobenzonitrile + H2O
3-fluorobenzamide
-
above 99.9% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
?
3-hydroxypropionitrile + H2O
3-hydroxypropanamide
-
35% of the activity with propionitrile
-
-
?
3-methoxybenzonitrile + H2O
3-methoxybenzamide
-
3% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
?
3-phenoxymandelonitrile + H2O
3-phenoxymandelamine
at 10% the rate of 2-hydroxy-4-phenylbutyronitrile
-
-
?
3-phenylpropanenitrile + H2O
3-phenylpropanamide
-
99.9% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
ir
3-phenylpropionitrile + H2O
3-phenylpropionamide
-
used as well as phenylacetonitrile
-
-
?
4-(trifluoromethyl)benzonitrile + H2O
4-(trifluoromethyl)benzamide
-
above 99.9% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
ir
4-acetylbenzonitrile + H2O
4-acetylbenzamide
-
above 99% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
ir
4-chloro-3-hydroxybutyronitrile + H2O
4-chloro-3-hydroxybutyramide
-
the following reaction by an amidase leads to the correspondend carboxylic acid
-
-
?
4-chlorobenzaldehyde + HCN + H2O
? + H2O
-
-
100% conversion to alpha-hydroxy nitrile
-
?
4-cyanobenzaldehyde + HCN + H2O
? + H2O
-
-
100% conversion to alpha-hydroxy nitrile
-
?
4-fluorobenzonitrile + H2O
4-fluorobenzamide
-
above 99.9% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
?
4-hydroxybenzaldehyde + HCN + H2O
? + H2O
-
-
55% conversion to alpha-hydroxy nitrile
-
?
4-methoxybenzonitrile + H2O
4-methoxybenzamide
-
above 99% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
ir
4-methylbenzaldehyde + HCN + H2O
? + H2O
-
-
51% conversion to alpha-hydroxy nitrile
-
?
4-methylbenzonitrile + H2O
4-methylbenzamide
-
above 99.9% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
ir
4-methylmandelonitrile + H2O
4-methylmandelamine
at 60% the rate of 2-hydroxy-4-phenylbutyronitrile
-
-
?
4-nitrobenzaldehyde + HCN + H2O
? + H2O
-
-
100% conversion to alpha-hydroxy nitrile
-
?
5-cyanovaleric acid + H2O
6-amino-6-oxohexanoic acid
-
NilFe and NilCo
-
-
r
acetamiprid + H2O
(1E)-N'-carbamoyl-N-[(6-chloropyridin-3-yl)methyl]-N-methylethanimidamide
hydration at 22.41% compared to the activity with thiacloprid
-
-
?
aeroplysinin-1 + H2O
verongiaquinol
-
high substrate specificity towards the physiological substrate aeroplysinin-1
-
-
?
benzaldehyde + HCN
? + H2O
-
-
95% conversion to alpha-hydroxy nitrile
-
?
benzyl cyanide + H2O
2-phenylacetamide
85% of the activity compared to 3-cyanopyridine
-
-
?
ethyl 3-cyanobenzoate + H2O
ethyl 3-carbamoylbenzoate
-
no conversion, in phosphate buffer pH 7.0, at 30°C
-
-
?
ethyl 4-cyanobenzoate + H2O
ethyl 4-carbamoylbenzoate
-
95% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
ir
furan-2-carbonitrile + H2O
furan-2-carboxamide
-
99.9% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
ir
hexanedinitrile + H2O
?
hydration at 0.43% compared to the activity with thiacloprid
-
-
?
malononitrile + 2 H2O
malonamide
the use of the wild-type enzyme leads to malonamide formation with 97.3% malononitrile conversion. Variants Y68T and W72Y show a drastic change in regiospecificity by producing mainly the omega-cyanocarboxamide, cyanoacetamide, at a relatively low malononitrile conversion. Mutant enzyme Y68T/W72Y produces 97.1% omega-cyanocarboxamide
-
-
?
malononitrile + H2O
cyanoacetamide
the use of the wild-type enzyme leads to malonamide formation with 97.3% malononitrile conversion. Variants Y68T and W72Y show a drastic change in regiospecificity by producing mainly the omega-cyanocarboxamide, cyanoacetamide, at a relatively low malononitrile conversion. Mutant enzyme Y68T/W72Y produces 97.1% omega-cyanocarboxamide
-
-
r
methyl 4-cyanobenzoate + H2O
methyl 4-carbamoylbenzoate
-
98% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
ir
phenylacetonitrile + H2O
2-phenylacetamide
-
28% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
ir
phthalodinitrile + 2 H2O
phthalamide
the wild-type enzyme forms 100% phthalamide from phthalodinitrile. The mutant enzymes Y68T and W72Y result in a higher 2-cyanobenzamide formation than their parent enzyme. Mutant enzyme Y68T/W72Y produces 100% 2-cyanobenzamide from phthalodinitrile
-
-
?
phthalodinitrile + H2O
2-cyanobenzamide
the wild-type enzyme forms 100% phthalamide from phthalodinitrile. The mutant enzymes Y68T and W72Y result in a higher 2-cyanobenzamide formation than their parent enzyme. Mutant enzyme Y68T/W72Y produces 100% 2-cyanobenzamide from phthalodinitrile
-
-
?
pyridine-2-carbonitrile + H2O
pyridine-2-carboxamide
-
99.9% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
ir
pyridine-4-carbonitrile + H2O
pyridine-4-carboxamide
-
99.9% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
ir
terephthalonitrile + 2 H2O
terephthalamide
the wild-type enzyme prefers terephthalonitrile to catalyze mainly into terephthalamide (84.3%) with a conversion up to 99.2 %. Variants Y68T and W72Y show a change in regiospecificity by producing mainly the 4-cyanobenzamide. Mutant enzyme Y68T/W72Y produces 98.2% 4-cyanobenzamide from terephthalonitrile
-
-
?
terephthalonitrile + H2O
4-cyanobenzamide
the wild-type enzyme prefers terephthalonitrile to catalyze mainly into terephthalamide (84.3%) with a conversion up to 99.2 %. Variants Y68T and W72Y show a change in regiospecificity by producing mainly the 4-cyanobenzamide. Mutant enzyme Y68T/W72Y produces 98.2% 4-cyanobenzamide from terephthalonitrile
-
-
?
thiacloprid + H2O
1-[(2Z)-3-[(6-chloropyridin-3-yl)methyl]-1,3-thiazolidin-2-ylidene]urea
-
-
-
?
thiophen-2-ylacetonitrile + H2O
2-(thiophen-2-yl)acetamide
-
89% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
ir
thiophene-2-carbonitrile + H2O
thiophene-2-carboxamide
-
99.9% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
?
trans-4-cyanocyclohexane-1-carboxylic acid + H2O
4-(aminocarbonyl)cyclohexanecarboxylic acid
(1R,3R)-2,2-dibromo-3-phenylcyclopropanecarbonitrile + H2O
(1R,3R)-2,2-dibromo-3-phenylcyclopropanecarbamide
-
substrate conversion: 11.6%, enantiomeric excess: 83.8, 88.9 (methanol), 81.0 (n-hexane)
-
-
r
(1R,3R)-2,2-dibromo-3-phenylcyclopropanecarbonitrile + H2O
(1R,3R)-2,2-dibromo-3-phenylcyclopropanecarbamide
-
substrate conversion: 11.6%, enantiomeric excess: 83.8, 88.9 (methanol), 81.0 (n-hexane)
-
-
r
(1R,3R)-3-phenylcyclopropanecarbonitrile + H2O
(1R,3R)-3-phenylcyclopropanecarbamide
-
substrate conversion: 49.1%, enantiomeric excess: 22.7, 31.1 (methanol), 21.6 (n-hexane)
-
-
r
(1R,3R)-3-phenylcyclopropanecarbonitrile + H2O
(1R,3R)-3-phenylcyclopropanecarbamide
-
substrate conversion: 49.1%, enantiomeric excess: 22.7, 31.1 (methanol), 21.6 (n-hexane)
-
-
r
(1R,3S)-3-phenylcyclopropanecarbonitrile + H2O
(1R,3S)-3-phenylcyclopropanecarbamide
-
substrate conversion: 25.8%, enantiomeric excess: 95.4, 95.4 (methanol), 95.5 (n-hexane)
-
-
r
(1R,3S)-3-phenylcyclopropanecarbonitrile + H2O
(1R,3S)-3-phenylcyclopropanecarbamide
-
substrate conversion: 25.8%, enantiomeric excess: 95.4, 95.4 (methanol), 95.5 (n-hexane)
-
-
r
(1S,3S)-2,2-dimethyl-3-phenylcyclopropanecarbonitrile + H2O
(1S,3S)-2,2-dimethyl-3-phenylcyclopropanecarbamide
-
substrate conversion: 40.3%, enantiomeric excess: 84.7
-
-
r
(1S,3S)-2,2-dimethyl-3-phenylcyclopropanecarbonitrile + H2O
(1S,3S)-2,2-dimethyl-3-phenylcyclopropanecarbamide
-
substrate conversion: 7.9%, enantiomeric excess: 3.2, 5.9 (methanol), 0.7 (n-hexane)
-
-
r
(R)-mandelonitrile + H2O
(R)-mandelamide
wild-type enzyme catalyzes the conversion of rac-mandelonitrile to (S)-mandelamide with an enantiomeric excess of 52.6%
-
-
?
(R)-mandelonitrile + H2O
(R)-mandelamide
wild-type enzyme catalyzes the conversion of rac-mandelonitrile to (S)-mandelamide with an enantiomeric excess of 52.6%
-
-
?
(S)-mandelonitrile + H2O
(S)-mandelamide
wild-type enzyme catalyzes the conversion of rac-mandelonitrile to (S)-mandelamide with an enantiomeric excess of 52.6%
-
-
?
(S)-mandelonitrile + H2O
(S)-mandelamide
wild-type enzyme catalyzes the conversion of rac-mandelonitrile to (S)-mandelamide with an enantiomeric excess of 52.6%
-
-
?
1,1,3,3,-tetramethylbutylisonitrile + H2O
1,1,3,3,-tetramethylisobutylamide
-
-
-
-
?
1,1,3,3,-tetramethylbutylisonitrile + H2O
1,1,3,3,-tetramethylisobutylamide
-
-
-
-
?
1-cyanocyclohexaneacetonitrile + H2O
1-cyanocyclohexaneacetamide
Rhodococcus aetherivorans JB1208
A0A2Z6FCE3; A0A2Z6FCD3
-
-
-
?
2(R)-(4-chlorophenyl)-3-methylbutyronitrile + H2O
2(R)-(4-chloro-phenyl)-3-methyl-butyramide
-
enantioselective hydration
-
?
2(R)-(4-chlorophenyl)-3-methylbutyronitrile + H2O
2(R)-(4-chloro-phenyl)-3-methyl-butyramide
-
enantioselective hydration
-
?
2(S)-(4-chlorophenyl)-3-methylbutyronitrile + H2O
2(S)-(4-chloro-phenyl)-3-methyl-butyramide
-
-
-
?
2(S)-(4-chlorophenyl)-3-methylbutyronitrile + H2O
2(S)-(4-chloro-phenyl)-3-methyl-butyramide
-
-
-
?
2(S)-(4-chlorophenyl)-3-methylbutyronitrile + H2O
2(S)-(4-chloro-phenyl)-3-methyl-butyramide
-
enantioselective hydration
-
?
2(S)-(4-chlorophenyl)-3-methylbutyronitrile + H2O
2(S)-(4-chloro-phenyl)-3-methyl-butyramide
-
-
-
?
2(S)-(4-chlorophenyl)-3-methylbutyronitrile + H2O
2(S)-(4-chloro-phenyl)-3-methyl-butyramide
-
enantioselective hydration
-
?
2,2-dimethylcyclopropanecarbonitrile + H2O
2,2-dimethylcyclopropanecarboxamide
Comamonas oleophilus
-
-
-
-
?
2,2-dimethylcyclopropanecarbonitrile + H2O
2,2-dimethylcyclopropanecarboxamide
-
-
-
-
?
2,2-dimethylcyclopropanecarbonitrile + H2O
2,2-dimethylcyclopropanecarboxamide
-
-
-
-
?
2,2-dimethylcyclopropanecarbonitrile + H2O
2,2-dimethylcyclopropanecarboxamide
-
-
-
-
?
2,2-dimethylcyclopropanecarbonitrile + H2O
2,2-dimethylcyclopropanecarboxamide
-
-
-
-
?
2,2-dimethylcyclopropanecarbonitrile + H2O
2,2-dimethylcyclopropanecarboxamide
-
-
-
-
?
2,2-dimethylcyclopropanecarbonitrile + H2O
?
29% of the activity compared to 3-cyanopyridine
-
-
?
2,6-difluorobenzonitrile + H2O
2,6-difluorobenzamide
-
-
-
-
?
2-amino-2,3-dimethylbutyronitrile + H2O
2-amino-2,3-dimethylbutyramide
-
-
-
-
?
2-amino-2,3-dimethylbutyronitrile + H2O
2-amino-2,3-dimethylbutyramide
-
-
-
-
?
2-amino-2,3-dimethylbutyronitrile + H2O
2-amino-2,3-dimethylbutyramide
-
-
-
-
?
2-amino-2,3-dimethylbutyronitrile + H2O
2-amino-2,3-dimethylbutyramide
-
-
-
-
?
2-amino-2,3-dimethylbutyronitrile + H2O
2-amino-2,3-dimethylbutyramide
-
-
-
-
?
2-amino-2,3-dimethylbutyronitrile + H2O
2-amino-2,3-dimethylbutyramide
-
-
-
-
?
2-amino-2,3-dimethylbutyronitrile + H2O
2-amino-2,3-dimethylbutyramide
-
-
-
-
?
2-amino-2,3-dimethylbutyronitrile + H2O
2-amino-2,3-dimethylbutyramide
-
-
-
-
?
2-amino-2,3-dimethylbutyronitrile + H2O
2-amino-2,3-dimethylbutyramide
-
-
-
-
?
2-amino-2,3-dimethylbutyronitrile + H2O
2-amino-2,3-dimethylbutyramide
-
-
-
-
?
2-amino-2,3-dimethylbutyronitrile + H2O
2-amino-2,3-dimethylbutyramide
Rhodococcus sp. N595
-
-
-
-
?
2-amino-2,3-dimethylbutyronitrile + H2O
2-amino-2,3-dimethylbutyramide
-
-
-
-
?
2-amino-2,3-dimethylbutyronitrile + H2O
2-amino-2,3-dimethylbutyramide
-
-
-
-
?
2-cyanobenzamide + H2O
benzene-1,2-dicarboxamide
-
-
-
?
2-cyanobenzamide + H2O
benzene-1,2-dicarboxamide
-
-
-
?
2-cyanopyridine + H2O
pyridine-2-carbamide
46% of the activity compared to 3-cyanopyridine
-
-
?
2-cyanopyridine + H2O
pyridine-2-carbamide
46% of the activity compared to 3-cyanopyridine
-
-
?
2-hydroxypropionitrile + H2O
2-hydroxypropionic acid amide
-
i.e. DL-lactonitrile
-
-
?
2-hydroxypropionitrile + H2O
2-hydroxypropionic acid amide
-
116% of the activity with propionitrile
-
-
?
2-phenylpropionitrile + H2O
2-phenylpropionamide
-
used as well as phenylacetonitrile
-
-
?
2-phenylpropionitrile + H2O
2-phenylpropionamide
-
the enzyme is not enantioselective with the compound
-
-
?
2-phenylpropionitrile + H2O
2-phenylpropionamide
-
the enzyme is not enantioselective with the compound
-
-
?
2-phenylpropionitrile + H2O
2-phenylpropionamide
-
the enzyme is highly enantioselective with the compound
-
-
?
2-phenylpropionitrile + H2O
2-phenylpropionamide
-
the enzyme is highly enantioselective with the compound
-
-
?
2-phenylpropionitrile + H2O
2-phenylpropionamide
-
the enzyme is highly enantioselective with the compound
-
-
?
3,4,5-trimethoxybenzonitrile + H2O
3,4,5-trimethoxybenzamide
-
conversion rate: 21.71%
-
-
?
3,4,5-trimethoxybenzonitrile + H2O
3,4,5-trimethoxybenzamide
-
conversion rate: 21.71%
-
-
?
3,4-dimethoxybenzonitrile + H2O
3,4-dimethoxybenzaldehyde + NH3
-
second step with amidase (EC 3.5.1.4)
-
-
?
3,4-dimethoxybenzonitrile + H2O
3,4-dimethoxybenzaldehyde + NH3
Rhodococcus sp. Novo SP361
-
second step with amidase (EC 3.5.1.4)
-
-
?
3-(1-cyanoethyl)benzoic acid + H2O
?
-
the enzyme is enantioselective with the compound
-
-
?
3-(1-cyanoethyl)benzoic acid + H2O
?
-
the enzyme is enantioselective with the compound
-
-
?
3-(1-cyanoethyl)benzoic acid + H2O
?
-
the enzyme is enantioselective with the compound
-
-
?
3-(trifluoromethyl)benzonitrile + H2O
3-(trifluoromethyl)benzamide
-
5% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
?
3-(trifluoromethyl)benzonitrile + H2O
3-(trifluoromethyl)benzamide
-
5% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
?
3-benzoyloxyglutaronitrile + H2O
(S)-3-benzoyloxy-4-cyanobutyramide
-
enantiomeric excess: 95%, 5 h
-
-
?
3-benzoyloxyglutaronitrile + H2O
(S)-3-benzoyloxy-4-cyanobutyramide
-
enantiomeric excess: 95%, 5 h
-
-
?
3-benzyloxyglutaronitrile + H2O
3-benzyloxy-4-cyanobutyramide
-
enantiomeric excess: 69%, 30 min
-
-
?
3-benzyloxyglutaronitrile + H2O
3-benzyloxy-4-cyanobutyramide
-
enantiomeric excess: 69%, 30 min
-
-
?
3-chlorobenzonitrile + H2O
3-chlorobenzamide
-
95% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
?
3-cyanopyridine + H2O
nicotinamide
-
NHase-AMase cascade system exploited in a continuous reactor configuration, including nitrile hydratase and amidase, EC 3.5.1.4, activity. Bioconversion to intermediate nicotinamide and further to nicotinic acid
-
-
?
3-cyanopyridine + H2O
nicotinamide
-
NHase-AMase cascade system exploited in a continuous reactor configuration, including nitrile hydratase and amidase, EC 3.5.1.4, activity. Bioconversion to intermediate nicotinamide and further to nicotinic acid
-
-
?
3-cyanopyridine + H2O
nicotinamide
-
NHase-AMase cascade system exploited in a continuous reactor configuration, including nitrile hydratase and amidase, EC 3.5.1.4, activity. Bioconversion to intermediate nicotinamide and further to nicotinic acid
-
-
?
3-cyanopyridine + H2O
nicotinamide
substrate of recombinant wild-type enzyme, not of mutant enzymes
-
-
?
3-cyanopyridine + H2O
nicotinamide
substrate of recombinant wild-type enzyme, not of mutant enzymes
-
-
?
3-cyanopyridine + H2O
nicotinamide
-
a step in the biosynthesis of nicotinamide, one of the important forms of vitamin B3
-
-
?
3-cyanopyridine + H2O
nicotinamide
-
a step in the biosynthesis of nicotinamide, one of the important forms of vitamin B3
-
-
?
3-cyanopyridine + H2O
pyridine-3-carbamide
-
-
-
?
3-cyanopyridine + H2O
pyridine-3-carbamide
-
-
-
?
3-cyanopyridine + H2O
pyridine-3-carbamide
-
-
i.e. nicotinamide
-
?
3-cyanopyridine + H2O
pyridine-3-carbamide
-
-
-
?
3-cyanopyridine + H2O
pyridine-3-carbamide
-
-
-
?
3-cyanopyridine + H2O
pyridine-3-carbamide
-
-
i.e. nicotinamide
?
3-cyanopyridine + H2O
pyridine-3-carbamide
-
-
-
?
3-cyanopyridine + H2O
pyridine-3-carbamide
-
-
i.e. nicotinamide
?
3-cyanopyridine + H2O
pyridine-3-carbamide
-
-
i.e. nicotinamide
?
3-cyanopyridine + H2O
pyridine-3-carbamide
-
-
i.e. nicotinamide
?
3-cyanopyridine + H2O
pyridine-3-carbamide
-
-
i.e. nicotinamide
?
3-cyanopyridine + H2O
pyridine-3-carbamide
-
-
i.e. nicotinamide
?
3-cyanopyridine + H2O
pyridine-3-carbamide
-
-
-
?
3-cyanopyridine + H2O
pyridine-3-carbamide
hydration at 5528% compared to the activity with thiacloprid
-
-
?
3-cyanopyridine + H2O
pyridine-3-carbamide
Sinorhizobium meliloti CGMCC 7333
hydration at 5528% compared to the activity with thiacloprid
-
-
?
3-cyanopyridine + H2O
pyridine-3-carbamide
a niacin precursor
-
-
?
3-cyanopyridine + H2O
pyridine-3-carboxamide
-
-
-
?
3-hydroxy-3-phenylpropionitrile + H2O
3-hydroxy-3-phenylpropionamide
-
-
-
-
?
3-hydroxy-3-phenylpropionitrile + H2O
3-hydroxy-3-phenylpropionamide
Rhodococcus sp. Novo SP361
-
-
-
-
?
3-hydroxybutryronitrile + H2O
3-hydroxybutyramide
-
yield 99%
-
?
3-hydroxybutryronitrile + H2O
3-hydroxybutyramide
-
yield 99%
-
?
3-hydroxypropionitrile + H2O
3-hydroxypropionamide
-
yield 100%
-
?
3-hydroxypropionitrile + H2O
3-hydroxypropionamide
-
yield 100%
-
?
3-hydroxyvaleronitrile + H2O
3-hydroxyvaleramide
-
yield 99%
-
?
3-hydroxyvaleronitrile + H2O
3-hydroxyvaleramide
-
yield 99%
-
?
3-methylbenzonitrile + H2O
3-methylbenzamide
-
17% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
?
4-bromobenzonitrile + H2O
4-bromobenzamide
-
above 99% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
?
4-chlorobenzonitrile + H2O
4-chlorobenzamide
-
above 99.9% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
?
4-cyanobenzamide + H2O
benzene-1,4-dicarboxamide
-
-
-
?
4-cyanobenzamide + H2O
benzene-1,4-dicarboxamide
-
-
-
?
4-cyanopyridine + H2O
isonicotinamide
74% of the activity compared to 3-cyanopyridine
-
-
?
4-cyanopyridine + H2O
isonicotinamide
74% of the activity compared to 3-cyanopyridine
-
-
?
4-cyanopyridine + H2O
isonicotinamide
substrate of recombinant wild-type enzyme, not of mutant enzymes
-
-
?
4-cyanopyridine + H2O
isonicotinamide
substrate of recombinant wild-type enzyme, not of mutant enzymes
-
-
?
4-hydroxybenzonitrile + H2O
4-hydroxybenzoic acid amide
-
-
-
-
?
5-hydroxymethyl-2-furonitrile + H2O
5-hydroxymethyl-2-furamide
-
-
-
-
?
5-hydroxymethyl-2-furonitrile + H2O
5-hydroxymethyl-2-furamide
-
-
-
-
?
acetonitrile + H2O
acetamide
-
10% of the activity with propionitrile
-
-
?
acetonitrile + H2O
acetamide
-
10% of the activity with propionitrile
-
-
?
acetonitrile + H2O
acetamide
-
substrate specificity: acetonitrile ~ propionitrile > acrylonitrile >> butyronitrile
-
-
r
acetonitrile + H2O
acetamide
-
79% of the activity with acrylonitrile
-
-
?
acetonitrile + H2O
acetamide
-
substrate specificity: acetonitrile ~ propionitrile > acrylonitrile >> butyronitrile
-
-
r
acetonitrile + H2O
acetamide
hydration at 29.02% compared to the activity with thiacloprid
-
-
?
acetonitrile + H2O
acetamide
Sinorhizobium meliloti CGMCC 7333
hydration at 29.02% compared to the activity with thiacloprid
-
-
?
acrylonitrile + H2O
2-propenoic acid amide
-
-
i.e. acrylic acid amide
r
acrylonitrile + H2O
2-propenoic acid amide
-
-
i.e. acrylic acid amide
?
acrylonitrile + H2O
2-propenoic acid amide
-
78% of the activity with propionitrile
i.e. acrylic acid amide
?
acrylonitrile + H2O
2-propenoic acid amide
-
-
i.e. acrylic acid amide
?
acrylonitrile + H2O
2-propenoic acid amide
-
-
i.e. acrylic acid amide
?
acrylonitrile + H2O
2-propenoic acid amide
-
-
i.e. acrylic acid amide
?
acrylonitrile + H2O
2-propenoic acid amide
-
-
i.e. acrylic acid amide
?
acrylonitrile + H2O
2-propenoic acid amide
-
-
i.e. acrylamide
-
?
acrylonitrile + H2O
2-propenoic acid amide
-
-
i.e. acrylic acid amide
?
acrylonitrile + H2O
2-propenoic acid amide
-
-
i.e. acrylic acid amide
?
acrylonitrile + H2O
2-propenoic acid amide
-
-
i.e. acrylic acid amide
?
acrylonitrile + H2O
2-propenoic acid amide
-
-
i.e. acrylic acid amide
?
acrylonitrile + H2O
acrylamide
79% of the activity compared to 3-cyanopyridine
-
-
?
acrylonitrile + H2O
acrylamide
79% of the activity compared to 3-cyanopyridine
-
-
?
acrylonitrile + H2O
acrylamide
analysis of the structure model of the enzyme-substrate complex and catalytic mechanism, overview
-
-
?
acrylonitrile + H2O
acrylamide
substrate of recombinant wild-type and mutant enzymes
-
-
?
acrylonitrile + H2O
acrylamide
-
stereoselective reaction
-
-
?
acrylonitrile + H2O
acrylamide
analysis of the structure model of the enzyme-substrate complex and catalytic mechanism, overview
-
-
?
acrylonitrile + H2O
acrylamide
substrate of recombinant wild-type and mutant enzymes
-
-
?
acrylonitrile + H2O
acrylamide
-
substrate specificity: acetonitrile ~ propionitrile > acrylonitrile >> butyronitrile
-
-
r
acrylonitrile + H2O
acrylamide
-
substrate specificity: acetonitrile ~ propionitrile > acrylonitrile >> butyronitrile
-
-
r
adiponitrile + 2 H2O
adipic acid amide
-
108% of the activity with propionitrile
-
-
?
adiponitrile + 2 H2O
adipic acid amide
wild-type enzyme forms only adipamide after a 4 h reaction. Y68T and W72Y mutations cause a significant shift in product formation and form primarily 5-cyanovaleramide. Mutant enzyme Y68T/W72Y produces 100% 5-cyanovaleramide
-
-
?
adiponitrile + 2 H2O
adipic acid amide
wild-type enzyme forms only adipamide after a 4 h reaction. Y68T and W72Y mutations cause a significant shift in product formation and form primarily 5-cyanovaleramide. Mutant enzyme Y68T/W72Y produces 100% 5-cyanovaleramide
-
-
?
adiponitrile + H2O
5-cyanovaleramide
wild-type enzyme forms only adipamide after a 4 h reaction. Y68T and W72Y mutations cause a significant shift in product formation and form primarily 5-cyanovaleramide. Mutant enzyme Y68T/W72Y produces 100% 5-cyanovaleramide
-
-
r
adiponitrile + H2O
5-cyanovaleramide
wild-type enzyme forms only adipamide after a 4 h reaction. Y68T and W72Y mutations cause a significant shift in product formation and form primarily 5-cyanovaleramide. Mutant enzyme Y68T/W72Y produces 100% 5-cyanovaleramide
-
-
r
alpha-methylbenzyl cyanide + H2O
2-phenylpropanamide
65% of the activity compared to 3-cyanopyridine
-
-
?
an aliphatic amide
a nitrile + H2O
-
ligand exchange reactions, overview
-
-
?
an aliphatic amide
a nitrile + H2O
-
ligand exchange reactions, overview
-
-
?
an aliphatic amide
a nitrile + H2O
-
ligand exchange reactions, overview
-
-
?
an aliphatic amide
a nitrile + H2O
-
ligand exchange reactions, overview
-
-
?
benzonitrile + H2O
benzamide
-
performed by a cascade bienzymatic reaction involving nitrile hydration and acyl transfer of the intermediate benzamide onto hydroxylamine. The first step is catalyzed by a cell-free extract from recombinant Escherichia coli strain expressing nitrile hydratase from Klebsiella oxytoca strain 38.1.2, the second step is cell-free extract from Rhodococcus erythropolis A4 amidase, EC 3.5.1.4
-
-
?
benzonitrile + H2O
benzamide
82% of the activity compared to 3-cyanopyridine
-
-
?
benzonitrile + H2O
benzamide
-
performed by a cascade bienzymatic reaction involving nitrile hydration and acyl transfer of the intermediate benzamide onto hydroxylamine. The first step is catalyzed by a cell-free extract from recombinant Escherichia coli strain expressing nitrile hydratase from Klebsiella oxytoca strain 38.1.2, the second step is cell-free extract from Rhodococcus erythropolis A4 amidase, EC 3.5.1.4
-
-
?
benzonitrile + H2O
benzamide
substrate of recombinant wild-type and mutant enzymes
-
-
?
benzonitrile + H2O
benzamide
substrate of recombinant wild-type and mutant enzymes
-
-
?
benzonitrile + H2O
benzamide
-
performed by a cascade bienzymatic reaction involving nitrile hydration and acyl transfer of the intermediate benzamide onto hydroxylamine. The first step is catalyzed by a cell-free extract from recombinant Escherichia coli strain expressing nitrile hydratase from Raoultella terrigena srain 77.1, the second step is a cell-free extract from Rhodococcus erythropolis A4 amidase, EC 3.5.1.4
-
-
?
benzonitrile + H2O
benzamide
-
performed by a cascade bienzymatic reaction involving nitrile hydration and acyl transfer of the intermediate benzamide onto hydroxylamine. The first step is catalyzed by a cell-free extract from recombinant Escherichia coli strain expressing nitrile hydratase from Raoultella terrigena srain 77.1, the second step is a cell-free extract from Rhodococcus erythropolis A4 amidase, EC 3.5.1.4
-
-
?
benzonitrile + H2O
benzamide
-
99.9% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
ir
benzonitrile + H2O
benzamide
-
99.9% conversion, in phosphate buffer pH 7.0, at 30°C
-
-
ir
benzonitrile + H2O
benzamide
hydration at 2532% compared to the activity with thiacloprid
-
-
?
benzonitrile + H2O
benzamide
Sinorhizobium meliloti CGMCC 7333
hydration at 2532% compared to the activity with thiacloprid
-
-
?
benzonitrile + H2O
benzoic acid amide
-
1.3% of the activity with propionitrile
-
-
?
benzonitrile + H2O
benzoic acid amide
-
15% of the activity with acrylonitrile
-
-
?
benzonitrile + H2O
benzoic acid amide
-
19.4% of the activity with acrylonitrile
-
-
?
benzonitrile + hydroxylamine + H2O
benzohydroxamic acid + NH3
-
-
-
-
?
benzonitrile + hydroxylamine + H2O
benzohydroxamic acid + NH3
-
performed by a cascade bienzymatic reaction involving nitrile hydration and acyl transfer of the intermediate benzamide onto hydroxylamine. The first step is catalyzed by a cell-free extract from Rhodococcus erythropolis A4 containing nitrile hydratase, the second step is a cell-free extract from Rhodococcus erythropolis A4 amidase, EC 3.5.1.4
-
-
?
benzonitrile + hydroxylamine + H2O
benzohydroxamic acid + NH3
-
-
-
-
?
benzonitrile + hydroxylamine + H2O
benzohydroxamic acid + NH3
-
performed by a cascade bienzymatic reaction involving nitrile hydration and acyl transfer of the intermediate benzamide onto hydroxylamine. The first step is catalyzed by a cell-free extract from Rhodococcus erythropolis A4 containing nitrile hydratase, the second step is a cell-free extract from Rhodococcus erythropolis A4 amidase, EC 3.5.1.4
-
-
?
butyronitrile + H2O
butyramide
248% of the activity compared to 3-cyanopyridine
-
-
?
butyronitrile + H2O
butyramide
-
substrate specificity: acetonitrile ~ propionitrile > acrylonitrile >> butyronitrile
-
-
r
butyronitrile + H2O
butyramide
-
substrate specificity: acetonitrile ~ propionitrile > acrylonitrile >> butyronitrile
-
-
r
chloroacetonitrile + H2O
chloroacetamide
-
42% of the activity with propionitrile
-
-
?
chloroacetonitrile + H2O
chloroacetamide
-
42% of the activity with propionitrile
-
-
?
crotononitrile + H2O
(E)-2-butenoic acid amide
-
19% of the activity with propionitrile
-
-
?
crotononitrile + H2O
(E)-2-butenoic acid amide
-
19% of the activity with propionitrile
-
-
?
crotononitrile + H2O
(E)-2-butenoic acid amide
-
19% of the activity with propionitrile
-
-
?
hydroxyacetonitrile + H2O
hydroxyacetamide
-
50% of the activity with propionitrile
-
?
indole-3-acetonitrile + H2O
(indol-3-yl)acetamide
-
-
-
-
?
indole-3-acetonitrile + H2O
(indole-3-yl)acetamide
hydration at 479.79% compared to the activity with thiacloprid
-
-
?
indole-3-acetonitrile + H2O
(indole-3-yl)acetamide
Sinorhizobium meliloti CGMCC 7333
hydration at 479.79% compared to the activity with thiacloprid
-
-
?
indole-3-acetonitrile + H2O
indole-3-acetamide
-
conversion rate: 34.44%
-
-
?
indole-3-nitrile + H2O
indole-3-acetamide
-
the nitrile hydratase produces only indole-3-acetamide, no indole-3-acetic acid
-
?
isobutyronitrile + H2O
isobutyramide
215% of the activity compared to 3-cyanopyridine
-
-
?
isobutyronitrile + H2O
isobutyramide
hydration at 3.78% compared to the activity with thiacloprid
-
-
?
isobutyronitrile + H2O
isobutyric acid amide
-
113% of the activity with propionitrile
-
-
?
isobutyronitrile + H2O
isobutyric acid amide
-
113% of the activity with propionitrile
-
-
?
isobutyronitrile + H2O
isobutyric acid amide
-
71% of the activity with acrylonitrile
-
-
?
isobutyronitrile + H2O
isobutyric acid amide
-
71% of the activity with acrylonitrile
-
-
?
isobutyronitrile + H2O
isobutyric acid amide
-
62.5% of the activity with acrylonitrile
-
-
?
isobutyronitrile + H2O
isobutyric acid amide
-
62.5% of the activity with acrylonitrile
-
-
?
isovaleronitrile + H2O
isovaleric acid amide
-
more active than trans-4-cyanocyclohexane-1-carboxylic acid as substrate
-
-
?
isovaleronitrile + H2O
isovaleric acid amide
-
-
product identification by liquid chromatography tandem mass spectrometry
-
?
isovaleronitrile + H2O
isovaleric acid amide
-
-
product identification by liquid chromatography tandem mass spectrometry
-
?
mandelonitrile + H2O
?
31% of the activity compared to 3-cyanopyridine
-
-
?
methacrylamide + H2O
?
-
causes the greatest induction of activity
-
-
?
methacrylamide + H2O
?
-
causes the greatest induction of activity
-
-
?
methacrylonitrile + H2O
methacrylamide
substrate of recombinant wild-type and mutant enzymes
-
-
?
methacrylonitrile + H2O
methacrylamide
substrate of recombinant wild-type and mutant enzymes
-
-
?
methacrylonitrile + H2O
methylacrylamide
96% of the activity compared to 3-cyanopyridine
-
-
?
methacrylonitrile + H2O
methylacrylic acid amide
-
53% of the activity with propionitrile
-
-
?
methacrylonitrile + H2O
methylacrylic acid amide
-
more active than trans-4-cyanocyclohexane-1-carboxylic acid as substrate
-
-
?
n-butyronitrile + H2O
n-butyric acid amide
-
33% of the activity with propionitrile
-
-
?
n-butyronitrile + H2O
n-butyric acid amide
-
140% of the activity with propionitrile
-
-
?
n-butyronitrile + H2O
n-butyric acid amide
-
33% of the activity with propionitrile
-
-
?
n-butyronitrile + H2O
n-butyric acid amide
-
140% of the activity with propionitrile
-
-
?
n-butyronitrile + H2O
n-butyric acid amide
-
-
-
-
?
n-capronitrile + H2O
n-hexanoic acid amide
-
46% of the activity with propionitrile
-
-
?
n-capronitrile + H2O
n-hexanoic acid amide
-
46% of the activity with propionitrile
-
-
?
naproxennitrile + H2O
?
-
the enzyme is enantioselective with the compound
-
-
?
naproxennitrile + H2O
?
-
the enzyme is enantioselective with the compound
-
-
?
naproxennitrile + H2O
?
-
the enzyme is enantioselective with the compound
-
-
?
phenylacetonitrile + H2O
phenylacetamide
-
337% activity compared to indole-3-acetonitrile
-
-
?
phenylacetonitrile + H2O
phenylacetamide
-
337% activity compared to indole-3-acetonitrile
-
-
?
phenylacetonitrile + H2O
phenylacetamide
-
337% activity compared to indole-3-acetonitrile
-
-
?
phenylacetonitrile + H2O
phenylacetamide
-
337% activity compared to indole-3-acetonitrile
-
-
?
pivalonitrile + H2O
2,2-dimethylpropionic acid amide
-
5.3% of the activity with propionitrile
-
-
?
pivalonitrile + H2O
2,2-dimethylpropionic acid amide
-
5% of the activity with propionitrile
-
-
?
pivalonitrile + H2O
2,2-dimethylpropionic acid amide
-
62% of the activity with acrylonitrile
-
-
?
pivalonitrile + H2O
2,2-dimethylpropionic acid amide
-
62% of the activity with acrylonitrile
-
-
?
propionitrile + H2O
propionamide
113% of the activity compared to 3-cyanopyridine
-
-
?
propionitrile + H2O
propionamide
-
substrate specificity: acetonitrile ~ propionitrile > acrylonitrile >> butyronitrile
-
-
r
propionitrile + H2O
propionamide
-
substrate specificity: acetonitrile ~ propionitrile > acrylonitrile >> butyronitrile
-
-
r
propionitrile + H2O
propionic acid amide
-
-
i.e. propionamide
?
propionitrile + H2O
propionic acid amide
-
17% of the activity with acrylonitrile
-
-
?
propionitrile + H2O
propionic acid amide
-
17% of the activity with acrylonitrile
-
-
?
propionitrile + H2O
propionic acid amide
-
-
-
-
?
propionitrile + H2O
propionic acid amide
-
10% of conversion in 24 h
i.e. propionamide
?
propionitrile + H2O
propionic acid amide
-
10% of conversion in 24 h
i.e. propionamide
?
propionitrile + H2O
propionic acid amide
-
64% of the activity with acrylonitrile
-
-
?
propionitrile + H2O
propionic acid amide
-
64% of the activity with acrylonitrile
-
-
?
succinonitrile + H2O
?
hydration at 13.17% compared to the activity with thiacloprid
-
-
?
succinonitrile + H2O
?
Sinorhizobium meliloti CGMCC 7333
hydration at 13.17% compared to the activity with thiacloprid
-
-
?
trans-4-cyanocyclohexane-1-carboxylic acid + H2O
4-(aminocarbonyl)cyclohexanecarboxylic acid
-
-
-
?
trans-4-cyanocyclohexane-1-carboxylic acid + H2O
4-(aminocarbonyl)cyclohexanecarboxylic acid
-
-
-
?
valeronitrile + H2O
n-pentanoic acid amide
-
2.7% of the activity with propionitrile
-
-
?
valeronitrile + H2O
n-pentanoic acid amide
-
2.7% of the activity with propionitrile
-
-
?
valeronitrile + H2O
n-pentanoic acid amide
-
more than 3 times more active than trans-4-cyanocyclohexane-1-carboxylic acid as substrate
-
-
?
valeronitrile + H2O
n-pentanoic acid amide
-
almost 9000fold higher activity towards valeronitrile compared to (R,S)-2-phenylpropionitrile
-
-
?
valeronitrile + H2O
n-pentanoic acid amide
Rhodococcus equi TG328-2
-
almost 9000fold higher activity towards valeronitrile compared to (R,S)-2-phenylpropionitrile
-
-
?
additional information
?
-
-
(indol-3-yl)acetamide is no substrate, no formation of iodoacetic acid
-
-
?
additional information
?
-
-
(indol-3-yl)acetamide is no substrate, no formation of iodoacetic acid
-
-
?
additional information
?
-
-
no activity with aeroplysinin-1 derivatives (1S,2R)-3,5-dibromo-1-(cyanomethyl)-4-methoxycyclohexa-3,5-diene-1,2-diyl diacetate, (2-hydroxy-4-methoxyphenyl)acetonitrile, and (3,5-dibromo-2-hydroxy-4-methoxyphenyl)acetonitrile
-
-
?
additional information
?
-
-
the enzyme acts on low-molecular aliphatic nitriles with 2-5 carbons but not on aliphatic nitriles with more than 6 carbons
-
-
?
additional information
?
-
-
aliphatic nitriles with more than 5 carbons and aromatic nitriles cannot act as substrate
-
-
?
additional information
?
-
-
aliphatic nitriles with more than 5 carbons and aromatic nitriles cannot act as substrate
-
-
?
additional information
?
-
-
an unusual preference for branched and cyclic aliphatic nitriles is noted
-
-
?
additional information
?
-
Corynebacterium nitrilophilus
-
highest rate of reaction with short chain aliphatic nitriles
-
-
?
additional information
?
-
-
substrate binding preferences and pK(a) determinations of a nitrile hydratase model complex, catalytic mechanism, overview
-
-
?
additional information
?
-
-
substrate specificity of strain 38.1.2, no activity with 4-tolunitrile, overview
-
-
?
additional information
?
-
recombinant NHaseK can hydrolyze a wide range of aliphatic, aromatic, and heterocyclic nitriles, and converts racemic nitriles to the corresponding S-amides, with E values ranging from 9 to 17
-
-
?
additional information
?
-
-
substrate specificity of strain 38.1.2, no activity with 4-tolunitrile, overview
-
-
?
additional information
?
-
recombinant NHaseK can hydrolyze a wide range of aliphatic, aromatic, and heterocyclic nitriles, and converts racemic nitriles to the corresponding S-amides, with E values ranging from 9 to 17
-
-
?
additional information
?
-
-
the NHase active site of the strain F28 might consist of cysteine and serine
-
-
?
additional information
?
-
-
the NHase active site of the strain F28 might consist of cysteine and serine
-
-
?
additional information
?
-
-
aromatic nitriles are barely hydrated by the enzyme
-
-
?
additional information
?
-
-
formamide, acetamide, acrylamide, propionamide, n-butyramide, isobutyramide, n-valeramide, succinamide, benzamide, phenylacetamide and lactamide are no substrates
-
-
?
additional information
?
-
-
methacrylamide-induced enzyme activity, no activity in absence of methacrylamide, no or reduced activity in NhpR transcriptional regulator defective mutants
-
-
?
additional information
?
-
-
aromatic nitriles are barely hydrated by the enzyme
-
-
?
additional information
?
-
-
formamide, acetamide, acrylamide, propionamide, n-butyramide, isobutyramide, n-valeramide, succinamide, benzamide, phenylacetamide and lactamide are no substrates
-
-
?
additional information
?
-
-
methacrylamide-induced enzyme activity, no activity in absence of methacrylamide, no or reduced activity in NhpR transcriptional regulator defective mutants
-
-
?
additional information
?
-
-
S enantiomer conversion is 14 times greater than the rate of R enantiomer conversion
-
-
?
additional information
?
-
-
roles of second- and third-shell residues of the active site structure in catalysis, overview. Three of the predicted second-shell residues, alpha-Asp164, beta-Glu56, and beta-His147, and one predicted third-shell residue, beta-His71, have significant effects on the catalytic efficiency of the enzyme, while one of the predicted residues, alpha-Glu168, and the three residues not predicted, alpha-Arg170, alpha-Tyr171, and beta-Tyr215, do not have any significant effects on the catalytic efficiency of the enzyme
-
-
?
additional information
?
-
the Fe-type NHase exhibits broad substrate specificity
-
-
?
additional information
?
-
-
S enantiomer conversion is 14 times greater than the rate of R enantiomer conversion
-
-
?
additional information
?
-
-
roles of second- and third-shell residues of the active site structure in catalysis, overview. Three of the predicted second-shell residues, alpha-Asp164, beta-Glu56, and beta-His147, and one predicted third-shell residue, beta-His71, have significant effects on the catalytic efficiency of the enzyme, while one of the predicted residues, alpha-Glu168, and the three residues not predicted, alpha-Arg170, alpha-Tyr171, and beta-Tyr215, do not have any significant effects on the catalytic efficiency of the enzyme
-
-
?
additional information
?
-
substrate specificity, overview
-
-
?
additional information
?
-
-
computational molecular dynamics modelling of ligand docking and substrate transport and binding, overview
-
-
?
additional information
?
-
-
NHase hydrates a nitrile to provide the corresponding amide product via an addition reaction of one water molecule, active site structure involving amidate nitrogen donors from the peptide backbone, overview
-
-
?
additional information
?
-
molecular modeling study of enzyme-substrate binding modes in the bi-enzyme pathway for degradation of nitrile to acid, specific residues within the enzyme's binding pockets formed diverse contacts with the substrate, molecular docking, overview. Top substrate having favorable interactions with nitrile hydratase is 3-cyanopyridine
-
-
?
additional information
?
-
the enzyme shows a preference for aromatic nitriles as substrates rather than aliphatic ones. Tryptophan residue betaTrp72 may be involved in substrate binding
-
-
?
additional information
?
-
the enzyme shows a preference for aromatic nitriles as substrates rather than aliphatic ones. Tryptophan residue betaTrp72 may be involved in substrate binding
-
-
?
additional information
?
-
-
NHase hydrates a nitrile to provide the corresponding amide product via an addition reaction of one water molecule, active site structure involving amidate nitrogen donors from the peptide backbone, overview
-
-
?
additional information
?
-
-
computational molecular dynamics modelling of ligand docking and substrate transport and binding, overview
-
-
?
additional information
?
-
substrate specificity, overview
-
-
?
additional information
?
-
molecular modeling study of enzyme-substrate binding modes in the bi-enzyme pathway for degradation of nitrile to acid, specific residues within the enzyme's binding pockets formed diverse contacts with the substrate, molecular docking, overview. Top substrate having favorable interactions with nitrile hydratase is 3-cyanopyridine
-
-
?
additional information
?
-
the enzyme shows a preference for aromatic nitriles as substrates rather than aliphatic ones. Tryptophan residue betaTrp72 may be involved in substrate binding
-
-
?
additional information
?
-
the enzyme shows a preference for aromatic nitriles as substrates rather than aliphatic ones. Tryptophan residue betaTrp72 may be involved in substrate binding
-
-
?
additional information
?
-
-
the thermoactive nitrilase from Pyrococcus abyssi hydrolyses small aliphatic nitriles like fumaro- and malononitril, docking calculations for fumaro- and malononitriles, modelling, overview
-
-
?
additional information
?
-
-
substrate specificity of strain 77.1, no activity with 4-tolunitrile and 3-chlorobenzonitrile, overview
-
-
?
additional information
?
-
-
substrate specificity of strain 77.1, no activity with 4-tolunitrile and 3-chlorobenzonitrile, overview
-
-
?
additional information
?
-
-
besides aromatic and heterocyclic nitriles, aliphatic ones are hydrated preferentially
-
-
?
additional information
?
-
-
no activity with (R,S)-2-(4-isobutylphenyl)propionitrile and (R,S)-3-(1-cyanoethyl)benzoic acid
-
-
?
additional information
?
-
-
structural and mechanistic insights from electron paramagnetic resonance and density functional theory studies
-
-
?
additional information
?
-
Rhodococcus equi TG328-2
-
structural and mechanistic insights from electron paramagnetic resonance and density functional theory studies
-
-
?
additional information
?
-
Rhodococcus equi TG328-2
-
besides aromatic and heterocyclic nitriles, aliphatic ones are hydrated preferentially
-
-
?
additional information
?
-
Rhodococcus equi TG328-2
-
no activity with (R,S)-2-(4-isobutylphenyl)propionitrile and (R,S)-3-(1-cyanoethyl)benzoic acid
-
-
?
additional information
?
-
substrate specificity, overview
-
-
?
additional information
?
-
molecular modeling study of enzyme-substrate binding modes in the bi-enzyme pathway for degradation of nitrile to acid, specific residues within the enzyme's binding pockets form diverse contacts with the substrate, molecular docking, overview. Top substrate having favorable interactions with nitrile hydratase is benzonitrile
-
-
?
additional information
?
-
-
analysis of enzyme enantioselectivity against a broad range of nitrile substrates, overview. The enzyme is aselective with a range of different 2-phenylacetonitriles. At least one bulky group in close proximity to the alpha-position of the chiral nitriles seems to be necessary for enantioselectivity of NHases. Nitrile groups attached to a quaternary carbon atom are only reluctantly accepted and show no selectivity
-
-
?
additional information
?
-
-
no activity with chloroxynil amide
-
-
?
additional information
?
-
-
no activity with chloroxynil amide
-
-
?
additional information
?
-
-
analysis of enzyme enantioselectivity against a broad range of nitrile substrates, overview. The enzyme is aselective with a range of different 2-phenylacetonitriles. At least one bulky group in close proximity to the alpha-position of the chiral nitriles seems to be necessary for enantioselectivity of NHases. Nitrile groups attached to a quaternary carbon atom are only reluctantly accepted and show no selectivity
-
-
?
additional information
?
-
substrate specificity, overview
-
-
?
additional information
?
-
-
substrate specificity, overview
-
-
?
additional information
?
-
molecular modeling study of enzyme-substrate binding modes in the bi-enzyme pathway for degradation of nitrile to acid, specific residues within the enzyme's binding pockets form diverse contacts with the substrate, molecular docking, overview. Top substrate having favorable interactions with nitrile hydratase is benzonitrile
-
-
?
additional information
?
-
-
molecular modeling study of enzyme-substrate binding modes in the bi-enzyme pathway for degradation of nitrile to acid, specific residues within the enzyme's binding pockets form diverse contacts with the substrate, molecular docking, overview. Top substrate having favorable interactions with nitrile hydratase is benzonitrile
-
-
?
additional information
?
-
-
H-NHase acts preferentially on aliphatic nitriles, while L-NHase has a higher affinity for aromatic nitriles
-
-
?
additional information
?
-
-
NhhG forms a complex with the alpha-subunit of H-NHase. NhhAG is very similar to the mediator of L-NHase, NhlAE, which is a heterotrimer complex consisting of the cobalt-containing alpha-subunit of L-NHase and NhlE
-
-
?
additional information
?
-
-
no activity with 2,6-dichlorobenzamide and dichlobenil acid
-
-
?
additional information
?
-
-
NhhG forms a complex with the alpha-subunit of H-NHase. NhhAG is very similar to the mediator of L-NHase, NhlAE, which is a heterotrimer complex consisting of the cobalt-containing alpha-subunit of L-NHase and NhlE
-
-
?
additional information
?
-
-
H-NHase acts preferentially on aliphatic nitriles, while L-NHase has a higher affinity for aromatic nitriles
-
-
?
additional information
?
-
-
no activity with 2,6-dichlorobenzamide and dichlobenil acid
-
-
?
additional information
?
-
-
no detectably transformation with 2-methyl-2-butenenitrile, benzonitrile and phenylacetonitrile
-
-
?
additional information
?
-
-
NHase is a non-heme iron enzyme catalyzing the hydration of various nitriles to the corresponding amides
-
-
?
additional information
?
-
-
hydrogen bonds between betaArg56 and alphaCys114 sulfenic acid are important to maintain the enzymatic activity, molecular dynamics simulations determining the differences in the dynamics of lightactive and dark-inactive forms of NHase, overview
-
-
?
additional information
?
-
-
NHase is a non-heme iron enzyme catalyzing the hydration of various nitriles to the corresponding amides
-
-
?
additional information
?
-
-
no detectably transformation with 2-methyl-2-butenenitrile, benzonitrile and phenylacetonitrile
-
-
?
additional information
?
-
-
the nitrile hydratase can hydrate aliphatic, aromatic and heterocyclic nitriles under very mild conditions, in mixtures of pH 7 buffer and a range of organic solvents, often with excellent chemoselectivity. Major determinant of hydration occurring is the degree of steric hindrance around the nitrile moiety and/or size of the substrates
-
-
?
additional information
?
-
-
analysis of enzyme enantioselectivity against a broad range of nitrile substrates, overview. At least one bulky group in close proximity to the alpha-position of the chiral nitriles seems to be necessary for enantioselectivity of NHases. Nitrile groups attached to a quaternary carbon atom are only reluctantly accepted and show no selectivity
-
-
?
additional information
?
-
-
the nitrile hydratase can hydrate aliphatic, aromatic and heterocyclic nitriles under very mild conditions, in mixtures of pH 7 buffer and a range of organic solvents, often with excellent chemoselectivity. Major determinant of hydration occurring is the degree of steric hindrance around the nitrile moiety and/or size of the substrates
-
-
?
additional information
?
-
-
analysis of enzyme enantioselectivity against a broad range of nitrile substrates, overview. At least one bulky group in close proximity to the alpha-position of the chiral nitriles seems to be necessary for enantioselectivity of NHases. Nitrile groups attached to a quaternary carbon atom are only reluctantly accepted and show no selectivity
-
-
?
additional information
?
-
-
analysis of enzyme enantioselectivity against a broad range of nitrile substrates, overview. At least one bulky group in close proximity to the alpha-position of the chiral nitriles seems to be necessary for enantioselectivity of NHases. Nitrile groups attached to a quaternary carbon atom are only reluctantly accepted and show no selectivity
-
-
?
additional information
?
-
substrate specificity of trimeric enzyme compared to the isolated alpha-subunit, overview. Activity of the alpha-subunit of a nitrile hydratase distinguishes among possible mechanisms of nitrile hydration by adding significant weight to those that rely solely on residues derived from the alpha-subunit. No activity with thiocyanate
-
-
?
additional information
?
-
substrate specificity of trimeric enzyme compared to the isolated alpha-subunit, overview. Activity of the alpha-subunit of a nitrile hydratase distinguishes among possible mechanisms of nitrile hydration by adding significant weight to those that rely solely on residues derived from the alpha-subunit. No activity with thiocyanate
-
-
?
additional information
?
-
substrate specificity of trimeric enzyme compared to the isolated alpha-subunit, overview. Activity of the alpha-subunit of a nitrile hydratase distinguishes among possible mechanisms of nitrile hydration by adding significant weight to those that rely solely on residues derived from the alpha-subunit. No activity with thiocyanate
-
-
?
additional information
?
-
-
substrate specificity of trimeric enzyme compared to the isolated alpha-subunit, overview. Activity of the alpha-subunit of a nitrile hydratase distinguishes among possible mechanisms of nitrile hydration by adding significant weight to those that rely solely on residues derived from the alpha-subunit. No activity with thiocyanate
-
-
?
